AU2021349262A1 - Piperazine-based cationic lipids - Google Patents

Info

Publication number

AU2021349262A1

AU2021349262A1 AU2021349262A AU2021349262A AU2021349262A1 AU 2021349262 A1 AU2021349262 A1 AU 2021349262A1 AU 2021349262 A AU2021349262 A AU 2021349262A AU 2021349262 A AU2021349262 A AU 2021349262A AU 2021349262 A1 AU2021349262 A1 AU 2021349262A1

Authority

AU

Australia

Prior art keywords

compound

optionally substituted

pharmaceutically acceptable

acceptable salt

alkyl

Prior art date

2020-09-23

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 125000002091 cationic group Chemical group 0.000 title claims description 91
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title abstract description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 298
• -1 lipid compounds Chemical class 0.000 claims abstract description 234
• 150000003839 salts Chemical class 0.000 claims abstract description 204
• 108020004999 messenger RNA Proteins 0.000 claims abstract description 104
• 238000012384 transportation and delivery Methods 0.000 claims abstract description 74
• 102000004169 proteins and genes Human genes 0.000 claims abstract description 54
• 108090000623 proteins and genes Proteins 0.000 claims abstract description 53
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 35
• 201000010099 disease Diseases 0.000 claims abstract description 27
• 150000002632 lipids Chemical class 0.000 claims description 189
• 239000000203 mixture Substances 0.000 claims description 149
• 239000002105 nanoparticle Substances 0.000 claims description 65
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 60
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 59
• 150000007523 nucleic acids Chemical class 0.000 claims description 46
• 102000039446 nucleic acids Human genes 0.000 claims description 43
• 108020004707 nucleic acids Proteins 0.000 claims description 43
• 238000000034 method Methods 0.000 claims description 37
• 108090000765 processed proteins & peptides Proteins 0.000 claims description 34
• 235000012000 cholesterol Nutrition 0.000 claims description 30
• 239000002502 liposome Substances 0.000 claims description 30
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 22
• 210000004072 lung Anatomy 0.000 claims description 20
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 17
• 125000002252 acyl group Chemical group 0.000 claims description 16
• 238000011282 treatment Methods 0.000 claims description 15
• 210000004185 liver Anatomy 0.000 claims description 12
• 238000005538 encapsulation Methods 0.000 claims description 11
• 230000002685 pulmonary effect Effects 0.000 claims description 8
• 208000008425 Protein deficiency Diseases 0.000 claims description 6
• 238000002663 nebulization Methods 0.000 claims description 6
• 210000004556 brain Anatomy 0.000 claims description 5
• 210000003205 muscle Anatomy 0.000 claims description 4
• 238000002560 therapeutic procedure Methods 0.000 claims description 4
• 208000023275 Autoimmune disease Diseases 0.000 claims description 3
• 208000035473 Communicable disease Diseases 0.000 claims description 3
• 206010028980 Neoplasm Diseases 0.000 claims description 3
• 201000011510 cancer Diseases 0.000 claims description 3
• 208000015181 infectious disease Diseases 0.000 claims description 3
• 230000002265 prevention Effects 0.000 claims description 3
• 208000035475 disorder Diseases 0.000 abstract description 8
• 230000007812 deficiency Effects 0.000 abstract description 4
• 125000000217 alkyl group Chemical group 0.000 description 160
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 101
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 99
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 93
• 125000003342 alkenyl group Chemical group 0.000 description 77
• 125000004432 carbon atom Chemical group C* 0.000 description 74
• 125000000304 alkynyl group Chemical group 0.000 description 68
• 125000005842 heteroatom Chemical group 0.000 description 60
• 125000000623 heterocyclic group Chemical group 0.000 description 60
• 125000003118 aryl group Chemical group 0.000 description 58
• 125000004452 carbocyclyl group Chemical group 0.000 description 58
• 239000000243 solution Substances 0.000 description 55
• 230000015572 biosynthetic process Effects 0.000 description 53
• 238000003786 synthesis reaction Methods 0.000 description 53
• 210000004027 cell Anatomy 0.000 description 50
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
• 125000001072 heteroaryl group Chemical group 0.000 description 39
• 239000011541 reaction mixture Substances 0.000 description 39
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 37
• 238000004458 analytical method Methods 0.000 description 37
• 238000006243 chemical reaction Methods 0.000 description 37
• 235000019439 ethyl acetate Nutrition 0.000 description 37
• 210000001519 tissue Anatomy 0.000 description 36
• 239000003921 oil Substances 0.000 description 35
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 34
• 125000001424 substituent group Chemical group 0.000 description 34
• 239000003981 vehicle Substances 0.000 description 31
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 30
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• 108091033319 polynucleotide Proteins 0.000 description 27
• 239000002157 polynucleotide Substances 0.000 description 27
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 26
• 239000012230 colorless oil Substances 0.000 description 26
• 229940024606 amino acid Drugs 0.000 description 25
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
• 229910052757 nitrogen Inorganic materials 0.000 description 24
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
• 150000001413 amino acids Chemical class 0.000 description 23
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
• 239000012044 organic layer Substances 0.000 description 22
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 21
• 229910052938 sodium sulfate Inorganic materials 0.000 description 21
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 20
• 239000000741 silica gel Substances 0.000 description 20
• 229910002027 silica gel Inorganic materials 0.000 description 20
• 235000011152 sodium sulphate Nutrition 0.000 description 20
• 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 19
• 125000000753 cycloalkyl group Chemical group 0.000 description 19
• 229910052717 sulfur Chemical group 0.000 description 19
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 18
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• 229910052760 oxygen Inorganic materials 0.000 description 18
• 239000001301 oxygen Substances 0.000 description 18
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 17
• 108020004414 DNA Proteins 0.000 description 17
• 102000053602 DNA Human genes 0.000 description 17
• 241000282414 Homo sapiens Species 0.000 description 17
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 17
• 239000011593 sulfur Chemical group 0.000 description 17
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 16
• 229910052698 phosphorus Inorganic materials 0.000 description 16
• 238000010898 silica gel chromatography Methods 0.000 description 16
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 15
• 238000001727 in vivo Methods 0.000 description 15
• 239000008194 pharmaceutical composition Substances 0.000 description 15
• 239000011574 phosphorus Chemical group 0.000 description 15
• 102000004196 processed proteins & peptides Human genes 0.000 description 15
• 238000005160 1H NMR spectroscopy Methods 0.000 description 14
• NSMWYRLQHIXVAP-UHFFFAOYSA-N 2,5-dimethylpiperazine Chemical compound CC1CNC(C)CN1 NSMWYRLQHIXVAP-UHFFFAOYSA-N 0.000 description 14
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 14
• 241001465754 Metazoa Species 0.000 description 14
• XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 14
• 229910052796 boron Inorganic materials 0.000 description 14
• 229910052710 silicon Inorganic materials 0.000 description 14
• 239000010703 silicon Chemical group 0.000 description 14
• 125000006732 (C1-C15) alkyl group Chemical group 0.000 description 13
• 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 description 13
• 239000000463 material Substances 0.000 description 13
• 230000008569 process Effects 0.000 description 13
• 229920002477 rna polymer Polymers 0.000 description 13
• 239000004055 small Interfering RNA Substances 0.000 description 13
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
• 125000004122 cyclic group Chemical group 0.000 description 12
• 239000003480 eluent Substances 0.000 description 12
• 238000009472 formulation Methods 0.000 description 12
• 238000001890 transfection Methods 0.000 description 12
• 239000012267 brine Substances 0.000 description 11
• 229910052736 halogen Inorganic materials 0.000 description 11
• 150000002367 halogens Chemical class 0.000 description 11
• 229920001184 polypeptide Polymers 0.000 description 11
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
• 239000000126 substance Substances 0.000 description 11
• 230000001225 therapeutic effect Effects 0.000 description 11
• 239000004743 Polypropylene Substances 0.000 description 10
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• 238000000605 extraction Methods 0.000 description 10
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• 210000005265 lung cell Anatomy 0.000 description 10
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• 229920001343 polytetrafluoroethylene Polymers 0.000 description 10
• 239000000047 product Substances 0.000 description 10
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 9
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 9
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• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 9
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
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• 125000004433 nitrogen atom Chemical group N* 0.000 description 9
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• 150000003254 radicals Chemical class 0.000 description 9
• 230000002829 reductive effect Effects 0.000 description 9
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 8
• 125000005915 C6-C14 aryl group Chemical group 0.000 description 8
• 125000001931 aliphatic group Chemical group 0.000 description 8
• 239000002585 base Substances 0.000 description 8
• MWRBNPKJOOWZPW-CLFAGFIQSA-N dioleoyl phosphatidylethanolamine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCCCC MWRBNPKJOOWZPW-CLFAGFIQSA-N 0.000 description 8
• 125000004404 heteroalkyl group Chemical group 0.000 description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
• PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 8
• 125000003729 nucleotide group Chemical group 0.000 description 8
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• 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
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• 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 7
• 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
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• WJURPNDDCYXIJZ-UHFFFAOYSA-N CCCCCCC(OCCCCC1OC1)=O Chemical compound CCCCCCC(OCCCCC1OC1)=O WJURPNDDCYXIJZ-UHFFFAOYSA-N 0.000 description 6
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• HMCKOYOTNVWSBV-UHFFFAOYSA-N hex-5-enyl heptanoate Chemical compound CCCCCCC(=O)OCCCCC=C HMCKOYOTNVWSBV-UHFFFAOYSA-N 0.000 description 6
• 238000000338 in vitro Methods 0.000 description 6
• GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 6
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